Triethylamine → HCID 25018892、化合物

HRID 1878712ノート

反応式

HRID 1878712 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH2:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[Br:14][C:15]1[CH:16]=[CH:17][C:18](=[O:25])[N:19]([CH2:21][C:22](O)=[O:23])[CH:20]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[Br:14][C:15]1[CH:16]=[CH:17][C:18](=[O:25])[N:19]([CH2:21][C:22]([NH:13][C:7]2[C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=[CH:9][CH:8]=2)=[O:23])[CH:20]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 167788012-(5-Bromo-2-oxopyridin-1(2H)-yl)acetic acidHCID 170398707-Methoxyquinolin-4-amine

生成物 1

HCID 25018892HCID 25018892、化合物収率 12.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

To a solution of 7-methoxyquinolin-4-amine (0.275 g, 2 mmol) and 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetic acid (0.273 g, 1 mmol) in 5 mL of DMF at rt was added triethylamine (0.2 ml, 2 mmol) followed by HATU (0.7 g, 2 mmol) solid. The reaction was then heated up to 40° C. for 8 hours and was cooled to rt and diluted with 60 mL of EtOAc and 30 mL of satd. NaHCO3 solution. The organic phase was separated, washed with 30 mL of brine and dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc to 10% MeOH/EtOAc) to give a white solid (0.05 g, 11% yield). MS (ESI pos. ion) m/z (MH+): 388.0. Calc'd Exact Mass for C17H14BrN3O3: 387.02.

後処理

  1. temperaturewas cooled to rt
  2. customThe organic phase was separated
  3. washwashed with 30 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (EtOAc to 10% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-1d056b744fa448988d359847e6bcceb4
出典データセット
uspto-grants-2012_11
特許番号
US08314087B2

反応ノート

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